data_an2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N2' _chemical_formula_weight 272.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6360(1) _cell_length_b 10.1513(1) _cell_length_c 14.2933(2) _cell_angle_alpha 92.812(1) _cell_angle_beta 91.680(1) _cell_angle_gamma 92.388(1) _cell_volume 1394.56(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prisms _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10003 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6315 _reflns_number_gt 4531 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+0.1973P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.033(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6315 _refine_ls_number_parameters 508 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.071 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.72111(11) 0.30432(10) 0.43684(8) 0.0289(3) Uani 1 1 d . . . C2 C 0.70606(15) 0.17184(13) 0.42647(10) 0.0321(3) Uani 1 1 d . . . C3 C 0.59963(15) 0.10655(13) 0.37387(10) 0.0319(3) Uani 1 1 d . . . N4 N 0.49871(11) 0.16930(10) 0.32865(7) 0.0297(3) Uani 1 1 d . . . C5 C 0.51316(13) 0.29985(12) 0.33880(8) 0.0246(3) Uani 1 1 d . . . C6 C 0.42136(13) 0.39768(12) 0.30130(9) 0.0252(3) Uani 1 1 d . . . C7 C 0.48818(13) 0.52538(12) 0.33466(9) 0.0253(3) Uani 1 1 d . . . C8 C 0.60549(12) 0.50978(11) 0.38676(8) 0.0232(3) Uani 1 1 d . . . C9 C 0.62312(13) 0.36732(12) 0.39119(8) 0.0240(3) Uani 1 1 d . . . C10 C 0.34129(14) 0.37095(13) 0.20735(9) 0.0284(3) Uani 1 1 d . . . C11 C 0.32664(16) 0.47974(14) 0.14030(10) 0.0333(3) Uani 1 1 d . . . C12 C 0.24088(14) 0.59051(14) 0.17495(10) 0.0329(3) Uani 1 1 d . . . C13 C 0.17261(14) 0.59140(14) 0.25388(10) 0.0338(3) Uani 1 1 d . . . C14 C 0.17041(15) 0.48278(14) 0.32071(10) 0.0321(3) Uani 1 1 d . . . C15 C 0.26286(13) 0.37089(13) 0.29510(9) 0.0277(3) Uani 1 1 d . . . C16 C 0.70093(13) 0.61465(12) 0.42931(8) 0.0235(3) Uani 1 1 d . . . C17 C 0.84355(13) 0.59686(13) 0.43737(9) 0.0264(3) Uani 1 1 d . . . C18 C 0.93392(15) 0.69728(13) 0.47454(9) 0.0295(3) Uani 1 1 d . . . C19 C 0.88261(15) 0.81639(13) 0.50571(9) 0.0313(3) Uani 1 1 d . . . C20 C 0.74109(15) 0.83500(13) 0.49939(9) 0.0300(3) Uani 1 1 d . . . C21 C 0.65088(14) 0.73560(12) 0.46122(9) 0.0262(3) Uani 1 1 d . . . H2 H 0.7758(15) 0.1213(13) 0.4594(9) 0.034(4) Uiso 1 1 d . . . H3 H 0.5951(14) 0.0090(14) 0.3677(10) 0.037(4) Uiso 1 1 d . . . H7 H 0.4505(13) 0.6103(12) 0.3192(9) 0.024(3) Uiso 1 1 d . . . H10 H 0.3612(13) 0.2821(13) 0.1798(9) 0.028(3) Uiso 1 1 d . . . H11A H 0.4204(16) 0.5153(14) 0.1253(10) 0.040(4) Uiso 1 1 d . . . H11B H 0.2832(15) 0.4401(14) 0.0793(11) 0.040(4) Uiso 1 1 d . . . H12 H 0.2329(15) 0.6659(14) 0.1320(10) 0.040(4) Uiso 1 1 d . . . H13 H 0.1160(15) 0.6671(14) 0.2720(10) 0.041(4) Uiso 1 1 d . . . H14A H 0.1950(14) 0.5189(13) 0.3855(10) 0.033(4) Uiso 1 1 d . . . H14B H 0.0743(17) 0.4480(14) 0.3225(10) 0.046(4) Uiso 1 1 d . . . H5 H 0.2339(14) 0.2847(13) 0.3171(9) 0.030(4) Uiso 1 1 d . . . H17 H 0.8798(13) 0.5127(13) 0.4174(9) 0.025(3) Uiso 1 1 d . . . H18 H 1.0340(16) 0.6805(13) 0.4811(10) 0.037(4) Uiso 1 1 d . . . H19 H 0.9451(15) 0.8853(14) 0.5353(10) 0.034(4) Uiso 1 1 d . . . H20 H 0.7023(14) 0.9169(14) 0.5257(10) 0.035(4) Uiso 1 1 d . . . H21 H 0.5485(15) 0.7482(13) 0.4562(9) 0.031(4) Uiso 1 1 d . . . N1' N 0.24451(11) 0.00520(10) 0.13725(7) 0.0306(3) Uani 1 1 d . . . C2' C 0.24200(15) -0.05036(14) 0.22095(10) 0.0330(3) Uani 1 1 d . . . C3' C 0.14024(15) -0.03024(13) 0.28494(10) 0.0318(3) Uani 1 1 d . . . N4' N 0.03239(12) 0.04744(10) 0.27009(7) 0.0295(3) Uani 1 1 d . . . C5' C 0.03409(13) 0.10225(12) 0.18786(8) 0.0254(3) Uani 1 1 d . . . C6' C -0.06677(13) 0.19100(12) 0.14984(9) 0.0264(3) Uani 1 1 d . . . C7' C -0.01305(13) 0.22235(13) 0.05783(9) 0.0268(3) Uani 1 1 d . . . C8' C 0.10613(13) 0.15979(12) 0.04011(8) 0.0249(3) Uani 1 1 d . . . C9' C 0.13818(13) 0.08264(12) 0.12169(9) 0.0248(3) Uani 1 1 d . . . C10' C -0.14040(13) 0.28752(13) 0.21610(9) 0.0281(3) Uani 1 1 d . . . C11' C -0.16563(15) 0.42572(13) 0.18698(10) 0.0301(3) Uani 1 1 d . . . C12' C -0.27326(14) 0.43280(14) 0.11008(9) 0.0321(3) Uani 1 1 d . . . C13' C -0.34627(15) 0.32984(14) 0.07112(10) 0.0333(3) Uani 1 1 d . . . C14' C -0.33235(15) 0.19010(14) 0.09749(10) 0.0323(3) Uani 1 1 d . . . C15' C -0.22136(13) 0.17171(13) 0.17183(9) 0.0276(3) Uani 1 1 d . . . C16' C 0.19007(13) 0.17016(12) -0.04399(9) 0.0252(3) Uani 1 1 d . . . C17' C 0.33212(14) 0.15092(13) -0.04015(10) 0.0303(3) Uani 1 1 d . . . C18' C 0.41127(16) 0.16356(14) -0.11903(10) 0.0350(3) Uani 1 1 d . . . C19' C 0.34918(15) 0.19596(13) -0.20275(10) 0.0336(3) Uani 1 1 d . . . C20' C 0.20786(16) 0.21418(13) -0.20824(10) 0.0338(3) Uani 1 1 d . . . C21' C 0.12875(15) 0.20153(13) -0.12956(9) 0.0297(3) Uani 1 1 d . . . H2' H 0.3189(15) -0.1082(13) 0.2367(10) 0.035(4) Uiso 1 1 d . . . H3' H 0.1438(14) -0.0744(13) 0.3448(10) 0.033(4) Uiso 1 1 d . . . H7' H -0.0600(14) 0.2852(13) 0.0170(9) 0.032(4) Uiso 1 1 d . . . H10' H -0.1091(14) 0.2781(13) 0.2815(10) 0.030(4) Uiso 1 1 d . . . H11D H -0.1973(14) 0.4798(13) 0.2435(10) 0.035(4) Uiso 1 1 d . . . H11C H -0.0778(16) 0.4685(14) 0.1677(10) 0.036(4) Uiso 1 1 d . . . H12' H -0.2908(15) 0.5239(14) 0.0882(10) 0.038(4) Uiso 1 1 d . . . H13' H -0.4175(16) 0.3426(14) 0.0207(10) 0.039(4) Uiso 1 1 d . . . H14C H -0.4246(17) 0.1574(15) 0.1250(11) 0.049(4) Uiso 1 1 d . . . H14D H -0.3168(15) 0.1316(14) 0.0418(11) 0.041(4) Uiso 1 1 d . . . H15' H -0.2370(13) 0.0942(13) 0.2111(9) 0.028(3) Uiso 1 1 d . . . H17' H 0.3740(15) 0.1225(13) 0.0188(11) 0.038(4) Uiso 1 1 d . . . H18' H 0.5127(17) 0.1475(14) -0.1146(11) 0.047(4) Uiso 1 1 d . . . H19' H 0.4038(15) 0.2022(14) -0.2592(11) 0.040(4) Uiso 1 1 d . . . H20' H 0.1631(15) 0.2370(14) -0.2677(11) 0.041(4) Uiso 1 1 d . . . H21' H 0.0268(16) 0.2134(13) -0.1336(10) 0.037(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0254(6) 0.0281(6) 0.0337(6) 0.0055(5) -0.0007(5) 0.0028(5) C2 0.0319(8) 0.0278(7) 0.0373(8) 0.0074(6) -0.0008(6) 0.0045(6) C3 0.0352(8) 0.0239(7) 0.0369(8) 0.0027(6) 0.0023(6) 0.0030(6) N4 0.0322(6) 0.0249(6) 0.0319(6) 0.0005(5) 0.0016(5) 0.0009(5) C5 0.0246(7) 0.0250(6) 0.0242(6) 0.0015(5) 0.0035(5) -0.0006(5) C6 0.0234(7) 0.0253(6) 0.0266(7) 0.0016(5) -0.0016(5) -0.0003(5) C7 0.0239(7) 0.0244(7) 0.0275(7) 0.0022(5) 0.0007(5) 0.0012(5) C8 0.0221(7) 0.0246(6) 0.0232(6) 0.0013(5) 0.0025(5) 0.0005(5) C9 0.0215(7) 0.0275(7) 0.0234(6) 0.0028(5) 0.0025(5) 0.0021(5) C10 0.0282(7) 0.0290(7) 0.0272(7) -0.0008(6) -0.0050(6) -0.0013(6) C11 0.0358(9) 0.0369(8) 0.0274(7) 0.0041(6) -0.0016(6) 0.0037(6) C12 0.0302(8) 0.0352(8) 0.0335(8) 0.0080(6) -0.0046(6) 0.0021(6) C13 0.0277(8) 0.0368(8) 0.0372(8) 0.0025(6) -0.0034(6) 0.0067(6) C14 0.0222(7) 0.0419(8) 0.0325(8) 0.0051(6) 0.0003(6) 0.0017(6) C15 0.0234(7) 0.0293(7) 0.0299(7) 0.0042(6) -0.0038(5) -0.0047(5) C16 0.0245(7) 0.0261(6) 0.0199(6) 0.0040(5) -0.0001(5) -0.0008(5) C17 0.0260(7) 0.0273(7) 0.0260(7) 0.0018(6) 0.0004(5) 0.0014(5) C18 0.0257(8) 0.0339(7) 0.0288(7) 0.0041(6) -0.0024(6) -0.0015(6) C19 0.0339(8) 0.0307(7) 0.0283(7) 0.0010(6) -0.0032(6) -0.0087(6) C20 0.0362(8) 0.0258(7) 0.0280(7) 0.0011(6) 0.0014(6) 0.0010(6) C21 0.0256(7) 0.0283(7) 0.0249(7) 0.0035(5) 0.0002(5) 0.0009(6) N1' 0.0302(6) 0.0309(6) 0.0306(6) -0.0001(5) -0.0020(5) 0.0048(5) C2' 0.0345(8) 0.0331(7) 0.0316(8) 0.0013(6) -0.0047(6) 0.0071(6) C3' 0.0393(8) 0.0291(7) 0.0269(7) 0.0018(6) -0.0038(6) 0.0024(6) N4' 0.0329(6) 0.0293(6) 0.0260(6) 0.0004(5) -0.0011(5) -0.0010(5) C5' 0.0272(7) 0.0243(6) 0.0240(6) -0.0022(5) -0.0009(5) -0.0020(5) C6' 0.0241(7) 0.0292(7) 0.0259(7) 0.0002(5) 0.0026(5) 0.0021(5) C7' 0.0268(7) 0.0274(7) 0.0260(7) 0.0002(6) -0.0003(5) 0.0015(6) C8' 0.0247(7) 0.0251(6) 0.0243(6) -0.0025(5) -0.0010(5) -0.0011(5) C9' 0.0251(7) 0.0234(6) 0.0251(6) -0.0030(5) -0.0026(5) -0.0012(5) C10' 0.0267(7) 0.0328(7) 0.0248(7) -0.0014(6) 0.0030(6) 0.0025(6) C11' 0.0305(8) 0.0285(7) 0.0310(7) -0.0032(6) 0.0025(6) 0.0010(6) C12' 0.0327(8) 0.0320(7) 0.0322(7) 0.0016(6) 0.0037(6) 0.0064(6) C13' 0.0287(8) 0.0384(8) 0.0328(7) -0.0009(6) -0.0008(6) 0.0056(6) C14' 0.0259(8) 0.0339(8) 0.0365(8) -0.0023(6) -0.0004(6) 0.0008(6) C15' 0.0250(7) 0.0284(7) 0.0296(7) 0.0004(6) 0.0044(5) 0.0011(5) C16' 0.0271(7) 0.0225(6) 0.0255(7) -0.0026(5) 0.0005(5) -0.0013(5) C17' 0.0274(7) 0.0355(7) 0.0275(7) -0.0013(6) 0.0005(6) -0.0003(6) C18' 0.0290(8) 0.0387(8) 0.0369(8) -0.0042(6) 0.0062(6) -0.0014(6) C19' 0.0401(9) 0.0312(7) 0.0291(7) -0.0015(6) 0.0101(6) -0.0040(6) C20' 0.0431(9) 0.0313(7) 0.0269(7) 0.0025(6) 0.0010(6) 0.0005(6) C21' 0.0306(8) 0.0286(7) 0.0297(7) -0.0002(6) 0.0005(6) 0.0010(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C9 1.3347(16) . ? N1 C2 1.3470(17) . ? C2 C3 1.3804(19) . ? C2 H2 0.985(14) . ? C3 N4 1.3507(17) . ? C3 H3 0.989(14) . ? N4 C5 1.3271(16) . ? C5 C9 1.4126(17) . ? C5 C6 1.4674(17) . ? C6 C7 1.4745(17) . ? C6 C10 1.5357(17) . ? C6 C15 1.5393(18) . ? C7 C8 1.3544(17) . ? C7 H7 0.982(12) . ? C8 C9 1.4673(17) . ? C8 C16 1.4735(17) . ? C10 C15 1.4833(19) . ? C10 C11 1.5056(19) . ? C10 H10 0.995(13) . ? C11 C12 1.496(2) . ? C11 H11A 0.992(16) . ? C11 H11B 1.013(15) . ? C12 C13 1.322(2) . ? C12 H12 1.008(15) . ? C13 C14 1.494(2) . ? C13 H13 0.990(14) . ? C14 C15 1.5101(19) . ? C14 H14A 0.998(14) . ? C14 H14B 0.979(16) . ? C15 H5 0.976(14) . ? C16 C17 1.3956(18) . ? C16 C21 1.3983(17) . ? C17 C18 1.3876(18) . ? C17 H17 0.969(13) . ? C18 C19 1.3838(19) . ? C18 H18 0.988(14) . ? C19 C20 1.385(2) . ? C19 H19 0.976(14) . ? C20 C21 1.3843(19) . ? C20 H20 0.988(14) . ? C21 H21 1.001(14) . ? N1' C9' 1.3372(15) . ? N1' C2' 1.3478(17) . ? C2' C3' 1.375(2) . ? C2' H2' 0.992(14) . ? C3' N4' 1.3485(17) . ? C3' H3' 0.986(14) . ? N4' C5' 1.3251(16) . ? C5' C9' 1.4120(18) . ? C5' C6' 1.4634(17) . ? C6' C7' 1.4717(18) . ? C6' C15' 1.5379(18) . ? C6' C10' 1.5384(17) . ? C7' C8' 1.3595(18) . ? C7' H7' 0.999(13) . ? C8' C9' 1.4687(17) . ? C8' C16' 1.4741(18) . ? C10' C15' 1.4875(18) . ? C10' C11' 1.5101(19) . ? C10' H10' 0.985(14) . ? C11' C12' 1.4954(19) . ? C11' H11D 1.016(14) . ? C11' H11C 0.988(15) . ? C12' C13' 1.3252(19) . ? C12' H12' 1.010(14) . ? C13' C14' 1.496(2) . ? C13' H13' 0.997(15) . ? C14' C15' 1.5090(19) . ? C14' H14C 1.031(17) . ? C14' H14D 0.989(15) . ? C15' H15' 0.998(13) . ? C16' C17' 1.3906(18) . ? C16' C21' 1.3992(18) . ? C17' C18' 1.3877(19) . ? C17' H17' 0.984(15) . ? C18' C19' 1.382(2) . ? C18' H18' 0.998(16) . ? C19' C20' 1.382(2) . ? C19' H19' 0.980(15) . ? C20' C21' 1.3851(19) . ? C20' H20' 0.984(15) . ? C21' H21' 0.995(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C2 113.63(11) . . ? N1 C2 C3 123.57(13) . . ? N1 C2 H2 116.4(8) . . ? C3 C2 H2 120.1(8) . . ? N4 C3 C2 123.27(12) . . ? N4 C3 H3 116.8(8) . . ? C2 C3 H3 119.9(8) . . ? C5 N4 C3 113.31(11) . . ? N4 C5 C9 123.70(11) . . ? N4 C5 C6 127.74(11) . . ? C9 C5 C6 108.55(10) . . ? C5 C6 C7 103.82(10) . . ? C5 C6 C10 121.16(10) . . ? C7 C6 C10 125.41(11) . . ? C5 C6 C15 120.67(11) . . ? C7 C6 C15 123.52(11) . . ? C10 C6 C15 57.68(8) . . ? C8 C7 C6 111.97(11) . . ? C8 C7 H7 125.5(7) . . ? C6 C7 H7 122.5(7) . . ? C7 C8 C9 107.12(11) . . ? C7 C8 C16 127.16(11) . . ? C9 C8 C16 125.70(11) . . ? N1 C9 C5 122.50(11) . . ? N1 C9 C8 128.95(11) . . ? C5 C9 C8 108.53(10) . . ? C15 C10 C11 120.85(12) . . ? C15 C10 C6 61.28(8) . . ? C11 C10 C6 120.19(11) . . ? C15 C10 H10 115.2(8) . . ? C11 C10 H10 116.9(7) . . ? C6 C10 H10 110.4(7) . . ? C12 C11 C10 114.48(12) . . ? C12 C11 H11A 109.4(8) . . ? C10 C11 H11A 109.1(8) . . ? C12 C11 H11B 108.9(8) . . ? C10 C11 H11B 108.3(8) . . ? H11A C11 H11B 106.4(12) . . ? C13 C12 C11 124.40(13) . . ? C13 C12 H12 119.9(8) . . ? C11 C12 H12 115.6(8) . . ? C12 C13 C14 124.94(13) . . ? C12 C13 H13 120.3(9) . . ? C14 C13 H13 114.7(9) . . ? C13 C14 C15 114.41(12) . . ? C13 C14 H14A 110.2(8) . . ? C15 C14 H14A 109.8(8) . . ? C13 C14 H14B 107.3(9) . . ? C15 C14 H14B 108.9(9) . . ? H14A C14 H14B 105.8(12) . . ? C10 C15 C14 120.55(12) . . ? C10 C15 C6 61.04(8) . . ? C14 C15 C6 118.39(11) . . ? C10 C15 H5 116.6(8) . . ? C14 C15 H5 115.7(8) . . ? C6 C15 H5 113.1(8) . . ? C17 C16 C21 118.31(11) . . ? C17 C16 C8 121.01(11) . . ? C21 C16 C8 120.67(11) . . ? C18 C17 C16 120.97(12) . . ? C18 C17 H17 119.6(8) . . ? C16 C17 H17 119.5(8) . . ? C19 C18 C17 119.94(13) . . ? C19 C18 H18 121.1(8) . . ? C17 C18 H18 118.9(8) . . ? C18 C19 C20 119.80(13) . . ? C18 C19 H19 120.2(8) . . ? C20 C19 H19 119.9(8) . . ? C21 C20 C19 120.38(12) . . ? C21 C20 H20 118.9(8) . . ? C19 C20 H20 120.6(8) . . ? C20 C21 C16 120.58(12) . . ? C20 C21 H21 120.9(7) . . ? C16 C21 H21 118.5(7) . . ? C9' N1' C2' 113.70(11) . . ? N1' C2' C3' 123.70(12) . . ? N1' C2' H2' 117.3(8) . . ? C3' C2' H2' 119.0(8) . . ? N4' C3' C2' 123.20(13) . . ? N4' C3' H3' 116.9(8) . . ? C2' C3' H3' 119.8(8) . . ? C5' N4' C3' 113.42(11) . . ? N4' C5' C9' 123.90(11) . . ? N4' C5' C6' 127.46(11) . . ? C9' C5' C6' 108.64(11) . . ? C5' C6' C7' 104.22(10) . . ? C5' C6' C15' 119.69(11) . . ? C7' C6' C15' 125.13(11) . . ? C5' C6' C10' 119.95(11) . . ? C7' C6' C10' 125.22(11) . . ? C15' C6' C10' 57.83(8) . . ? C8' C7' C6' 111.55(11) . . ? C8' C7' H7' 126.8(8) . . ? C6' C7' H7' 121.6(8) . . ? C7' C8' C9' 107.25(11) . . ? C7' C8' C16' 126.54(12) . . ? C9' C8' C16' 126.19(11) . . ? N1' C9' C5' 122.08(11) . . ? N1' C9' C8' 129.59(12) . . ? C5' C9' C8' 108.34(11) . . ? C15' C10' C11' 121.01(12) . . ? C15' C10' C6' 61.07(8) . . ? C11' C10' C6' 119.88(11) . . ? C15' C10' H10' 115.3(8) . . ? C11' C10' H10' 116.9(8) . . ? C6' C10' H10' 110.6(8) . . ? C12' C11' C10' 114.28(12) . . ? C12' C11' H11D 107.9(8) . . ? C10' C11' H11D 108.6(8) . . ? C12' C11' H11C 109.1(8) . . ? C10' C11' H11C 110.0(8) . . ? H11D C11' H11C 106.7(11) . . ? C13' C12' C11' 124.75(13) . . ? C13' C12' H12' 119.2(8) . . ? C11' C12' H12' 116.0(8) . . ? C12' C13' C14' 124.86(13) . . ? C12' C13' H13' 120.1(8) . . ? C14' C13' H13' 115.0(8) . . ? C13' C14' C15' 114.45(12) . . ? C13' C14' H14C 108.6(8) . . ? C15' C14' H14C 105.9(8) . . ? C13' C14' H14D 111.1(8) . . ? C15' C14' H14D 109.7(8) . . ? H14C C14' H14D 106.7(12) . . ? C10' C15' C14' 120.56(12) . . ? C10' C15' C6' 61.10(8) . . ? C14' C15' C6' 120.44(12) . . ? C10' C15' H15' 116.9(7) . . ? C14' C15' H15' 115.6(7) . . ? C6' C15' H15' 110.9(7) . . ? C17' C16' C21' 118.34(12) . . ? C17' C16' C8' 121.02(11) . . ? C21' C16' C8' 120.64(12) . . ? C18' C17' C16' 120.82(13) . . ? C18' C17' H17' 120.8(9) . . ? C16' C17' H17' 118.3(9) . . ? C19' C18' C17' 120.04(14) . . ? C19' C18' H18' 120.8(9) . . ? C17' C18' H18' 119.2(9) . . ? C20' C19' C18' 120.01(13) . . ? C20' C19' H19' 119.5(8) . . ? C18' C19' H19' 120.5(8) . . ? C19' C20' C21' 119.99(13) . . ? C19' C20' H20' 120.3(9) . . ? C21' C20' H20' 119.7(9) . . ? C20' C21' C16' 120.79(13) . . ? C20' C21' H21' 120.1(8) . . ? C16' C21' H21' 119.1(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C2 C3 -0.08(19) . . . . ? N1 C2 C3 N4 -1.0(2) . . . . ? C2 C3 N4 C5 0.87(19) . . . . ? C3 N4 C5 C9 0.26(18) . . . . ? C3 N4 C5 C6 -178.50(12) . . . . ? N4 C5 C6 C7 179.86(12) . . . . ? C9 C5 C6 C7 0.95(13) . . . . ? N4 C5 C6 C10 -32.4(2) . . . . ? C9 C5 C6 C10 148.73(12) . . . . ? N4 C5 C6 C15 36.06(19) . . . . ? C9 C5 C6 C15 -142.85(11) . . . . ? C5 C6 C7 C8 -0.47(14) . . . . ? C10 C6 C7 C8 -146.42(12) . . . . ? C15 C6 C7 C8 142.00(12) . . . . ? C6 C7 C8 C9 -0.19(14) . . . . ? C6 C7 C8 C16 178.23(11) . . . . ? C2 N1 C9 C5 1.20(18) . . . . ? C2 N1 C9 C8 179.59(12) . . . . ? N4 C5 C9 N1 -1.39(19) . . . . ? C6 C5 C9 N1 177.58(11) . . . . ? N4 C5 C9 C8 179.93(12) . . . . ? C6 C5 C9 C8 -1.10(14) . . . . ? C7 C8 C9 N1 -177.77(12) . . . . ? C16 C8 C9 N1 3.8(2) . . . . ? C7 C8 C9 C5 0.80(14) . . . . ? C16 C8 C9 C5 -177.64(11) . . . . ? C5 C6 C10 C15 108.84(13) . . . . ? C7 C6 C10 C15 -110.61(14) . . . . ? C5 C6 C10 C11 -140.20(13) . . . . ? C7 C6 C10 C11 0.4(2) . . . . ? C15 C6 C10 C11 110.96(14) . . . . ? C15 C10 C11 C12 6.20(19) . . . . ? C6 C10 C11 C12 -66.35(17) . . . . ? C10 C11 C12 C13 -5.4(2) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C12 C13 C14 C15 4.2(2) . . . . ? C11 C10 C15 C14 -2.19(19) . . . . ? C6 C10 C15 C14 107.73(13) . . . . ? C11 C10 C15 C6 -109.92(14) . . . . ? C13 C14 C15 C10 -2.98(18) . . . . ? C13 C14 C15 C6 68.35(16) . . . . ? C5 C6 C15 C10 -109.67(13) . . . . ? C7 C6 C15 C10 113.79(14) . . . . ? C5 C6 C15 C14 139.16(12) . . . . ? C7 C6 C15 C14 2.62(18) . . . . ? C10 C6 C15 C14 -111.17(14) . . . . ? C7 C8 C16 C17 -146.03(13) . . . . ? C9 C8 C16 C17 32.10(18) . . . . ? C7 C8 C16 C21 32.86(19) . . . . ? C9 C8 C16 C21 -149.00(12) . . . . ? C21 C16 C17 C18 -1.13(18) . . . . ? C8 C16 C17 C18 177.79(12) . . . . ? C16 C17 C18 C19 1.10(19) . . . . ? C17 C18 C19 C20 -0.2(2) . . . . ? C18 C19 C20 C21 -0.6(2) . . . . ? C19 C20 C21 C16 0.61(19) . . . . ? C17 C16 C21 C20 0.28(18) . . . . ? C8 C16 C21 C20 -178.65(11) . . . . ? C9' N1' C2' C3' 0.05(19) . . . . ? N1' C2' C3' N4' 0.0(2) . . . . ? C2' C3' N4' C5' 0.07(18) . . . . ? C3' N4' C5' C9' -0.25(18) . . . . ? C3' N4' C5' C6' 179.89(12) . . . . ? N4' C5' C6' C7' 179.29(12) . . . . ? C9' C5' C6' C7' -0.59(13) . . . . ? N4' C5' C6' C15' -34.84(18) . . . . ? C9' C5' C6' C15' 145.28(11) . . . . ? N4' C5' C6' C10' 32.91(19) . . . . ? C9' C5' C6' C10' -146.98(11) . . . . ? C5' C6' C7' C8' 0.54(14) . . . . ? C15' C6' C7' C8' -142.89(12) . . . . ? C10' C6' C7' C8' 144.58(12) . . . . ? C6' C7' C8' C9' -0.27(14) . . . . ? C6' C7' C8' C16' -178.67(11) . . . . ? C2' N1' C9' C5' -0.23(17) . . . . ? C2' N1' C9' C8' 179.50(12) . . . . ? N4' C5' C9' N1' 0.35(19) . . . . ? C6' C5' C9' N1' -179.76(11) . . . . ? N4' C5' C9' C8' -179.43(11) . . . . ? C6' C5' C9' C8' 0.46(14) . . . . ? C7' C8' C9' N1' -179.88(12) . . . . ? C16' C8' C9' N1' -1.5(2) . . . . ? C7' C8' C9' C5' -0.12(14) . . . . ? C16' C8' C9' C5' 178.28(11) . . . . ? C5' C6' C10' C15' -108.24(13) . . . . ? C7' C6' C10' C15' 112.83(14) . . . . ? C5' C6' C10' C11' 140.59(13) . . . . ? C7' C6' C10' C11' 1.66(19) . . . . ? C15' C6' C10' C11' -111.18(14) . . . . ? C15' C10' C11' C12' -1.67(18) . . . . ? C6' C10' C11' C12' 70.53(16) . . . . ? C10' C11' C12' C13' 2.3(2) . . . . ? C11' C12' C13' C14' -0.3(2) . . . . ? C12' C13' C14' C15' -2.4(2) . . . . ? C11' C10' C15' C14' -0.87(19) . . . . ? C6' C10' C15' C14' -110.25(14) . . . . ? C11' C10' C15' C6' 109.38(14) . . . . ? C13' C14' C15' C10' 2.81(19) . . . . ? C13' C14' C15' C6' -69.49(16) . . . . ? C5' C6' C15' C10' 108.68(13) . . . . ? C7' C6' C15' C10' -112.99(14) . . . . ? C5' C6' C15' C14' -140.88(12) . . . . ? C7' C6' C15' C14' -2.55(19) . . . . ? C10' C6' C15' C14' 110.44(14) . . . . ? C7' C8' C16' C17' 152.55(13) . . . . ? C9' C8' C16' C17' -25.55(19) . . . . ? C7' C8' C16' C21' -26.54(19) . . . . ? C9' C8' C16' C21' 155.35(12) . . . . ? C21' C16' C17' C18' 0.51(19) . . . . ? C8' C16' C17' C18' -178.61(12) . . . . ? C16' C17' C18' C19' 0.2(2) . . . . ? C17' C18' C19' C20' -0.8(2) . . . . ? C18' C19' C20' C21' 0.8(2) . . . . ? C19' C20' C21' C16' -0.1(2) . . . . ? C17' C16' C21' C20' -0.54(19) . . . . ? C8' C16' C21' C20' 178.58(12) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.220 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.039